EP1334967A1 - VERFAHREN ZUR HERSTELLUNG VON OPTISCH AKTIVEM (3R,5S,6E)-7-ç2-CYCLOPROPYL-4-(4-FLUORPHENYL)CHINOLIN-3-YL!-3,5-DIHYDROXY-6-HEPTENSÄUREETHYLESTER - Google Patents

VERFAHREN ZUR HERSTELLUNG VON OPTISCH AKTIVEM (3R,5S,6E)-7-ç2-CYCLOPROPYL-4-(4-FLUORPHENYL)CHINOLIN-3-YL!-3,5-DIHYDROXY-6-HEPTENSÄUREETHYLESTER Download PDF

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Publication number
EP1334967A1
EP1334967A1 EP01976679A EP01976679A EP1334967A1 EP 1334967 A1 EP1334967 A1 EP 1334967A1 EP 01976679 A EP01976679 A EP 01976679A EP 01976679 A EP01976679 A EP 01976679A EP 1334967 A1 EP1334967 A1 EP 1334967A1
Authority
EP
European Patent Office
Prior art keywords
carrier
cellulose tris
chlorophenyl carbamate
filler
quinolin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01976679A
Other languages
English (en)
French (fr)
Other versions
EP1334967A4 (de
Inventor
Atsushi Onishi
Koichi Murazumi
Kozo Tachibana
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daicel Corp
Nissan Chemical Corp
Original Assignee
Nissan Chemical Corp
Daicel Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nissan Chemical Corp, Daicel Chemical Industries Ltd filed Critical Nissan Chemical Corp
Publication of EP1334967A1 publication Critical patent/EP1334967A1/de
Publication of EP1334967A4 publication Critical patent/EP1334967A4/de
Withdrawn legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3268—Macromolecular compounds
    • B01J20/328—Polymers on the carrier being further modified
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
    • B01D15/3833—Chiral chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/29—Chiral phases
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
    • B01J20/3204—Inorganic carriers, supports or substrates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3268—Macromolecular compounds
    • B01J20/3272—Polymers obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
    • B01D15/1814—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns recycling of the fraction to be distributed
    • B01D15/1821—Simulated moving beds
    • B01D15/185—Simulated moving beds characterized by the components to be separated
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00—Aspects relating to sorbent materials
    • B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
    • B01J2220/54—Sorbents specially adapted for analytical or investigative chromatography
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Definitions

  • the present invention was made in the aforementioned circumstances.
  • the objective of this invention is to provide a process for producing optically active statins, especially optically active ethyl (3R, 5S, 6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6-heptenoate with higher separation productivity.
  • the filler which has adsorbed the strongly adsorbable substance, is contacted with a portion of extract as will be described below, the poorly adsorbable substance retained on the filler is expelled, and thus the adsorbable substance is concentrated.
  • Flow rate of eluent 7.87 ml/min. Step time: 1.5 min.
  • Concentration of feedstock 20 mg/ml-mobile phase
  • Flow rate in zone I 9.43 ml/min.
  • Flow rate in zone II 2.88 ml/min.
  • Flow rate in zone III 3.46 ml/min.
  • Flow rate in zone IV 1.56 ml/min.
  • k' (v-v0)/v0 wherein v0 is the retention volume of tri-tert-benzyl benzene, v is the retention volume of the solute.
  • W. Ex. 1 W. Ex. 2 C. Ex. 1 C. Ex.2 C. Ex. 3 Mobile phase Optical purity of raffinate (%ee) 99.5 99.4 - - 99.5 Optical purity of extract (%ee) 94.7 94.8 - - 94.6 Productivity (kg-rac./kg-CSP/day)*1 0.88 0.90 0.45 - 0.80

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Inorganic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Quinoline Compounds (AREA)
EP01976679A 2000-10-13 2001-10-12 VERFAHREN ZUR HERSTELLUNG VON OPTISCH AKTIVEM (3R,5S,6E)-7-ç2-CYCLOPROPYL-4-(4-FLUORPHENYL)CHINOLIN-3-YL]-3,5-DIHYDROXY-6-HEPTENSÄUREETHYLESTER Withdrawn EP1334967A4 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2000314245 2000-10-13
JP2000314245 2000-10-13
PCT/JP2001/009000 WO2002030903A1 (fr) 2000-10-13 2001-10-12 Procede de production d'ethyl (3r, 5s, 6e)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6-heptenoate actif sur le plan optique

Publications (2)

Publication Number Publication Date
EP1334967A1 true EP1334967A1 (de) 2003-08-13
EP1334967A4 EP1334967A4 (de) 2008-05-07

Family

ID=18793537

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01976679A Withdrawn EP1334967A4 (de) 2000-10-13 2001-10-12 VERFAHREN ZUR HERSTELLUNG VON OPTISCH AKTIVEM (3R,5S,6E)-7-ç2-CYCLOPROPYL-4-(4-FLUORPHENYL)CHINOLIN-3-YL]-3,5-DIHYDROXY-6-HEPTENSÄUREETHYLESTER

Country Status (7)

Country Link
US (1) US6946557B2 (de)
EP (1) EP1334967A4 (de)
JP (1) JP4236463B2 (de)
KR (1) KR100777553B1 (de)
CN (1) CN1204122C (de)
AU (1) AU2001295926A1 (de)
WO (1) WO2002030903A1 (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005033083A1 (en) * 2003-10-03 2005-04-14 Nissan Chemical Industries, Ltd. Process for producing high purity 3,5-dihydroxy-6-heptenoic acid derivative
US7258794B2 (en) 2002-10-09 2007-08-21 Daicel Chemical Industries, Ltd. Process for producing packing for resolving optical isomers
US7550596B2 (en) 2003-04-24 2009-06-23 Daicel Chemical Industries, Ltd. Method of producing ethyl (3R, 5S, 6E)-7-[2 cyclopropyl-4-(fluorophenyl) quinoline-3-yl]-3, 5-dihydroxy-6-heptenoate
EP2113769A1 (de) * 2007-02-23 2009-11-04 Daicel Chemical Industries, Ltd. Füller zur trennung optischer isomere

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7399409B2 (en) * 2000-10-13 2008-07-15 Daicel Chemical Industries, Ltd. Packing material for separation of optical isomer and method of separating optical isomer with the same
RU2260001C2 (ru) * 2001-04-05 2005-09-10 Ниссан Кемикал Индастриз, ЛТД Способ получения 7-хинолинил-3,5-дигидроксигепт-6-еноата
ZA200502325B (en) * 2002-09-20 2006-11-29 Nissan Chemical Ind Ltd Method for producing a 3,5-dihydroxy-6-heptenoate
EP1623976A4 (de) * 2003-04-24 2008-07-30 Daicel Chem Verfahren zur trennung optisch aktiver dihydroxyheptensäureester
WO2008088830A2 (en) * 2007-01-16 2008-07-24 Evolved Nanomaterial Sciences, Inc. Chiral separating agents with active support
US9481797B2 (en) 2011-08-09 2016-11-01 Cristal Usa Inc. Pigment for paper and paper laminate
CA2896800A1 (en) 2013-01-21 2014-07-24 Cala Health, Inc. Devices and methods for controlling tremor
EP3148640B1 (de) 2014-06-02 2024-01-24 Cala Health, Inc. Systeme für periphere nervenstimulation zur behandlung von tremor
CN112914514A (zh) 2015-06-10 2021-06-08 卡拉健康公司 用于外周神经刺激以利用可拆卸治疗和监测单元治疗震颤的系统和方法
WO2017053847A1 (en) 2015-09-23 2017-03-30 Cala Health, Inc. Systems and methods for peripheral nerve stimulation in the finger or hand to treat hand tremors
CN108778411B (zh) 2016-01-21 2022-06-03 卡拉健康公司 用来治疗与膀胱过动症相关的疾病的用于外周神经调制的系统、方法和装置
WO2018009680A1 (en) 2016-07-08 2018-01-11 Cala Health, Inc. Systems and methods for stimulating n nerves with exactly n electrodes and improved dry electrodes
US11331480B2 (en) 2017-04-03 2022-05-17 Cala Health, Inc. Systems, methods and devices for peripheral neuromodulation for treating diseases related to overactive bladder
US11857778B2 (en) 2018-01-17 2024-01-02 Cala Health, Inc. Systems and methods for treating inflammatory bowel disease through peripheral nerve stimulation
US11890468B1 (en) 2019-10-03 2024-02-06 Cala Health, Inc. Neurostimulation systems with event pattern detection and classification

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3289200B2 (ja) * 1993-08-04 2002-06-04 有光工業株式会社 混気洗浄装置
WO1995023125A1 (fr) 1994-02-25 1995-08-31 Daicel Chemical Industries, Ltd. Procede de production de compose de mevalonolactone optiquement actif

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
No further relevant documents disclosed *
See also references of WO0230903A1 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7258794B2 (en) 2002-10-09 2007-08-21 Daicel Chemical Industries, Ltd. Process for producing packing for resolving optical isomers
US7550596B2 (en) 2003-04-24 2009-06-23 Daicel Chemical Industries, Ltd. Method of producing ethyl (3R, 5S, 6E)-7-[2 cyclopropyl-4-(fluorophenyl) quinoline-3-yl]-3, 5-dihydroxy-6-heptenoate
WO2005033083A1 (en) * 2003-10-03 2005-04-14 Nissan Chemical Industries, Ltd. Process for producing high purity 3,5-dihydroxy-6-heptenoic acid derivative
US7692018B2 (en) 2003-10-03 2010-04-06 Nissan Chemical Industries, Ltd. Process for producing high purity 3,5-dihydroxy-6-heptenoic acid derivative
CN1845899B (zh) * 2003-10-03 2010-04-28 日产化学工业株式会社 高纯度3,5-二羟基-6-庚烯酸衍生物的制备方法
EP2113769A1 (de) * 2007-02-23 2009-11-04 Daicel Chemical Industries, Ltd. Füller zur trennung optischer isomere
EP2113769A4 (de) * 2007-02-23 2013-06-26 Daicel Chem Füller zur trennung optischer isomere

Also Published As

Publication number Publication date
US20050075502A1 (en) 2005-04-07
KR20030036793A (ko) 2003-05-09
AU2001295926A1 (en) 2002-04-22
WO2002030903A1 (fr) 2002-04-18
EP1334967A4 (de) 2008-05-07
CN1468223A (zh) 2004-01-14
US6946557B2 (en) 2005-09-20
KR100777553B1 (ko) 2007-11-16
JP4236463B2 (ja) 2009-03-11
JPWO2002030903A1 (ja) 2004-02-19
CN1204122C (zh) 2005-06-01

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Free format text: PROCESS FOR PRODUCING OPTICALLY ACTIVE ETHYL (3R,5S,6E)-7- 2-CYCLOPROPYL-4-(4-FLUOROPHENYL)QUINOLIN-3-YL -3,5-DIHYDROXY-6-HEPTENOATE

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Free format text: PROCESS FOR PRODUCING OPTICALLY ACTIVE ETHYL (3R,5S,6E)-7- 2-CYCLOPROPYL-4-(4-FLUOROPHENYL)QUINOLIN-3-YL -3,5-DIHYDROXY-6-HEPTENOATE

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